An email to my aunt & things to do in Portland, Maine.

portland-harbor-0I get paid to write about Maine and just as importantly, to know things about Maine. I write shopping guides and restaurant roundups, bar reviews and weekend trip planners. I write for local newspapers and magazines and sometimes for national publications. As a result, out-of-towners often ask me what they should experience while in Maine. I dole out restaurant recommendations on the regular, and I love doing it.

But here’s the thing: When I’m writing for a magazine or a newspaper or even a website, I always tailor my voice and my opinions to their audience. This isn’t unusual. This is what all writers do—we write toward our audience. Plus, editors are then hired to go over my words and ideas and shift them, orient them towards their intended audience. Often, three or four different people read my writing, tweaking it all along the way. It’s a great system, and one works well. Editors are wonderful beings, and I really respect their work.

But still, sometimes the final piece, the piece that goes to print, isn’t so much about what Katy Kelleher likes as it is about what Magazine X likes.

That’s why I’ve decided to share something here. It’s an email I wrote this week for my aunt. She was coming to Portland, and she’d never seen the city. I wanted her to have the best possible experience, so I emailed her a list of my favorite places to eat, see art, shop, and just generally hang out. I couldn’t spend the whole day with her, but I could try to shape her experience a little. And unlike most of my writing, this wasn’t meant for public consumption. The intended audience was just my aunt—my feminist, funny, smart, art-loving family member. I wasn’t trying to impress her—but I hoped that Portland would.

So here is my unfiltered, unpolished, unedited list of Portland recommendations:

Hi Kathleen,

Portland is really lovely. We have friends visiting during the day on Saturday, but we could meet you around 5 or 6 in the evening, if that is alright. (Maybe earlier if the weather isn’t great.)

I do suggest you take some time to explore Portland! Because it really is a beautiful city—and I feel kind of strongly about it, like I built it or something. It’s my city! And I love it.

Here are some things worth seeing…

South of Portland, on your way up, stop at Two Lights State Park

It’s also where Edward Hopper painted this pretty little gem

Once you’re in the city, the Portland Museum of Art is a wonderful place to spend some time. Designed by I.M. Pei, it’s a cool building with a great collection of art. Look for pieces by John Bisbee (his work is made entirely of nails and there are several in the sculpture garden—I’ve interviewed him a few times and he’s the freaking best. He’s brilliant and scary and awesome.) Also be sure to head upstairs to the top gallery where there’s a menagerie of flying birds and beasts. It’s an incredibly cool room. This museum is also where I gave my first-ever reading, so it’s special to me.

Nearby are two of my favorite bookstores: Yes Books and The Green Hand. Yes is packed with books, floor to ceiling, and has an amazing selection of used art books.

Also nearby is She Bear, a great art gallery that sells prints and other cool things

Also nearby is the Bearded Lady’s Jewel Box, one of the best bars in town. The cocktails here are the reason for coming. The bartender uses things like wild foraged herbs and chamomile syrups and white pine in his cocktails.

If it’s nice out, the Eastern Promenade is a nice place to walk for views of the ocean and sailboats.

Or, if you would rather see old mansions and interesting architecture (but less impressive water views) the Western Promenade is also wonderful. The graveyard nearby is quite picturesque. It’s also pretty historic (designed by Olmsted I think?)

I wrote this recently for the shopping site Racked. It’s an overview of Portland shopping, if that’s what you’re feeling. Reny’s is one of my top recommendations because it’s so Maine. They sell smoked oysters in tins and camping gear and clothes and cookies and snowshoes and shovels and basically everything you might ever need.

Food-wise, here are some of my favorite places:

For drinks (alcoholic and otherwise) and vintage midcentury modern glassware, visit Vena’s Fizz House

(I wrote about them for Old Port magazine)

Eventide Oyster Bar and the Honey Paw are right next to each other and are owned by James Beard-winning chefs. The food is expensive, but good.

My personal favorite restaurant is Local 188. I go there all the time. It’s friendly and relaxed and has big couches and a comfortable space.

For German food, Schulte and Herr is the best best best. It’s like stepping back into the 1970s into some German grandma’s kitchen. The potato pancakes are wonderful.

For coffee and pastries, nothing beats Tandem. Located on the West End (the congress street location—there’s another location but it doesn’t always have food). My favorite thing is the apple feta scone with dusted black pepper. The coffee is great, too. (Located near the Western Promenade.)

For lunch, Pai Men Miyake has the best ramen around

Another good lunch spot is Duckfat. It’s super famous (the chef’s always on TV for some reason or another). The french fries are fried in duck fat and are awesome. The sandwiches and salads are great, too. My mom always asks to go here. It’s her favorite. (Dan’s favorite is Pai Men Miyake because he likes the pork buns. My dad also likes it there because he’s all about Japanese food.)

Other things to see and do:
The Portland Observatory is neat, and Munjoy Hill is an up-and-coming neighborhood
The home goods at Angela Adams are excellent and nature-inspired and awesome.
The Portland Flea for All and Architectural Salvage are great for antiquing
Commercial Street is fun if you want to see a working wharf and smell the scent of herring wafting through the air and watch lobstermen unload their boats
The Old Port is all cobblestone streets and charm (that’s where Vena’s Fizz House is located, as well as many of the best shops, including Little, a wonderful boutique for babies…. that’s where I got Anni her presents!!!!)

So, as usual, I went a little overboard. But I wanted to give you and Tony some options for things to do in town. Portland is small, but it’s really great.I’m excited to see you both. If you’re thinking, “Oh, wow Katy that was helpful, except I really just wanted to find a place that has lobster guacamole and you really failed at giving me that crucial information” let me know. It’s literally MY JOB to know this shit, so I’m full of recommendations for everything.

Photograph by Erin Little for 


3 thoughts on “An email to my aunt & things to do in Portland, Maine.

  1. Hi there! My husband and I moved from Portland to Colorado a few years ago and just moved back home. My heart and soul belongs by the sea. Loved your email! I found it very helpful for new/old places to explore.

    1. I’m so glad it was useful! There’s a funny link between Maine people and Colorado people. When my husband and I were leaving Boston, we knew we wanted to try one of two places: Portland or Denver. It’s pure chance we ended up here, but I have several friends who moved out of Portland to Colorado in the past few years.

      1. You’re so right. When I was there, I lost count of how many Mainers I met. If you ever go for a visit, let me know. I’d be happy to recommend some places in the Northern Colorado area.

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